The Inn on Fleming

Key West, FL · Guest house

Rating
4.4/5
★★★★☆ 4.4
Reviews
20
Rank in Key West
#39
of 154 hotels
City Percentile
48%
rating percentile
Address
The Inn on Fleming, 1016 Fleming St, Key West, FL 33040
Phone
(305) 394-4944
Website
www.dwellkeywest.com/key-west-vacation-rentals/inn-fleming

The Inn on Fleming is a hotel located in Key West, FL. It is one of 154 hotels listed in Key West. Its 4.4-star rating matches the Key West city average of 4.3 stars. There are 10 photos associated with this location.

Customer Reviews

Stardancer6691 · Dec 2025

We are here now, and have the Simonton room, first floor. King-size bed, plenty of room for clothing and luggage, nice bathroom. We also have the run of this lovely old guest house - kitchen, dining area, sitting, area, front porch, small pool, back deck. We have a coffee maker, fridge and tabletop ice maker in our room. Full kitchen has microwave, toaster, glassware, mugs, full size fridge. Everything is well kept, very clean, and you have access to a virtual innkeeper by text, and virtual concierge. There are beach towels, bikes, and umbrellas to borrow. |Location is fabulous - quiet old section of town, but only a few blocks from the harbor, and only a few blocks from Duval. All are easy walkable. |Enjoy your coffee, or a glass of wine out on the porch. Bring back takeout, and dine in

★★★☆☆ 3.0 Kellin Cavanaugh · Aug 2025

TLDR; new management seems to lack care and attention to meaningful details. I wish there were specific categories for ownership and atmosphere. Other reviews list the same question I have, “where’s David?” This is our first time visiting since Dwell took over and it gave off the sterilization of a mgmt company after the buy out a private landlord. Much of the antiques, eclectic decor has been replaced by shabby wayfair products. Further, it felt like we were living through their renovation for half of our stay. Planks on the back deck had caved in by the lounge chairs, and so the entire area was blocked off for the majority of our stay. They also had an enormous ceiling leak right outside our door (Mallory room), that took three days to resolve—I understand that this is clearly an urge

707mariajosen · Jun 2025

I love this place. I think very reasonable price for the quality. I stayed in the Truman room from Sunday to Friday. It is not the typical hotel with a front desk. They communicate through text, and that’s ok because I only needed the key to enter my room. A girl that was here when I arrived gave me the key and explained the lock box. In my bedroom, I had a queen bed and four pillows that were very comfortable, and I have a “sleep number bed” at home. In the bedroom, you will find a small bathroom with a shower which is fine for one person. Nice big nightstand with a charger for all your electronics. One refrigerator, an ice maker which I really found useful to prepare my water to leave in the morning or night drinks. Also, a coffee maker although you have Old Town Bakery with good coffe

Sculthorpe-Pike · Jan 2025

Review of inn on Fleming||Downtown Key West is full of beautiful old timber houses with wraparound decks and the IoF is similar and very attractive. |It isn’t, however, an Inn. All the rooms, except the kitchen, are bedrooms, there’s no reception just lockboxes for your room key when you arrive, having been well briefed by the absent owners, by messenger|Don’t accept room ‘ Mallory‘ as it is the smallest and right next to the kitchen, with other guests banging around in there late at night and early morning which frustrates a good night’s sleep. |Also, whilst ‘breakfast’ is included, don’t get excited. It’s a typical ‘grab your own muffin/ bagel and make your own coffee’. If you want normal tea then bring your own milk - there’s only something called half and half which isn’t milk and isn’

dawndJ2449EK · May 2025

There appears to have been some recent change in management of this property. It is now managed by Dwell, maybe was previously privately owned? There was no sign of “David” who others have frequently mentioned in reviews. |First off, when you check in, there is nobody available to greet you or provide any direction. You are sent a text with instructions on how to find your room and there’s a lock box outside the door to get your keys. Prior reviews have mentioned a free, happy hour and continental breakfast. According to the new management, these are no longer provided.|We stayed in the Cornish room, which was on the third floor. The room is cute and well appointed. But the entryway ceiling is extremely low and if you are above about 5‘8“, you were going to hit your head if you’re not car

Accessibility & Amenities

✓ Lgbtq Friendly

Services

Guest houseInn

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